FIELD OF THE INVENTION
This invention is concerned with new organic compounds and more particularly with triazinobenzodiazepines and methods for the production thereof.
The new products of this invention and the process of production thereof can be illustratively represented by the following formulae: ##STR5## wherein R and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is hydrogen or alkyl as defined above; wherein R.sub.2 is hydrogen or methyl; wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl or 2-pyridyl; and wherein Y is chloro, bromo, iodo, or EQU --O--SO.sub.2 --R.sub.4
in which R.sub.4 is alkyl defined as above, phenyl or tolyl.
The invention encompasses besides the compounds of formula IV, the pharmacologically acceptable acid addition salts of these compounds.
The more desirable products of this invention have the formula IVa: ##STR6## wherein R'.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, wherein R'.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, and nitro, and wherein R.sub.4 is hydrogen, chloro, or fluoro, and the pharmacologically acceptable acid addition salts thereof.
The most desirable compounds of this invention are of the formula IVb: ##STR7## wherein R".sub.1 is hydrogen or methyl; wherein R.sub.4 is hydrogen, chloro, or fluoro; and wherein R".sub.3 is chloro, fluoro, and trifluoromethyl, and the pharmacologically acceptable acid addition salts thereof.
The process of the present invention comprises: treating a compound of formula I with a reagent of formula II to give the corresponding 2-(substituted-hydrazino)benzodiazepine III; and heating III to cyclize it to provide the final product IV.